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$102+ Cheap flights from O'Hare Intl (ORD) to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Portland are usually found in August or March, booked 57 days in advance, depart on a Tuesday or Sunday and return on a Thursday

Cheap flight deals from O'Hare Intl to Portland

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 18, 2025.

Round-trip from

$237
(JetBlue)

One-way from

$102
(JetBlue)

Popular in

November

Cheapest in

August

Average price

$307

Good round-trip deal

$284 or less

Good one-way deal

$156 or less
From Chicago O'Hare Intl to Portland
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One-way flight from Chicago O'Hare Intl to Portland
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Highest demand for flights based on searches. 12% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Portland.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Portland.
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Find flight deals from O'Hare Intl to Portland

Cheapest flights from O'Hare Intl to Portland
Explore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This JetBlue deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/111:36 pmORD - PWM
1 stop7h 31mJetBlue
Mon 9/152:17 pmPWM - ORD
1 stop7h 32mJetBlue
Deal found 8/16$237
This Expedia deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/189:42 amORD - PWM
2 stops11h 20mJetBlue
Wed 10/227:09 amPWM - ORD
1 stop6h 01mJetBlue
Deal found 8/15$239
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/108:15 amORD - PWM
Nonstop2h 34mAmerican Airlines
Wed 9/171:02 pmPWM - ORD
1 stop6h 59mAmerican Airlines
Deal found 8/17$241
This JetBlue deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/111:36 pmORD - PWM
1 stop7h 31mJetBlue
Tue 9/167:30 amPWM - ORD
1 stop5h 40mJetBlue
Deal found 8/17$243
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:30 pmORD - PWM
Nonstop2h 29mAmerican Airlines
Wed 10/16:20 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Deal found 8/17$245
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/310:05 amORD - PWM
1 stop9h 06mAmerican Airlines
Tue 9/96:01 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Deal found 8/18$247
This Priceline deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/161:36 pmORD - PWM
1 stop7h 26mJetBlue
Mon 10/202:17 pmPWM - ORD
1 stop7h 33mJetBlue
Deal found 8/15$248
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/318:50 amORD - PWM
1 stop4h 35mUnited Airlines
Thu 9/47:30 amPWM - ORD
1 stop5h 09mUnited Airlines
Deal found 8/16$249
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/133:45 pmORD - PWM
1 stop5h 15mDelta
Wed 9/176:33 amPWM - ORD
1 stop6h 43mDelta
Deal found 8/16$251
This CheapOair deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/51:36 pmORD - PWM
1 stop22h 46mJetBlue
Fri 9/122:17 pmPWM - ORD
1 stop27h 04mJetBlue
Deal found 8/16$253
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/26:45 pmORD - PWM
Nonstop2h 43mAmerican Airlines
Tue 9/96:00 amPWM - ORD
1 stop6h 06mAmerican Airlines
Deal found 8/17$255
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/133:45 pmORD - PWM
1 stop5h 15mDelta
Tue 9/166:00 amPWM - ORD
2 stops7h 35mDelta
Deal found 8/18$256

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland that are best for you.

Fly from

O'Hare Intl

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 9/11

1:36 pm-10:07 pm

1 stop7h 31m

Portland

Mon 9/15

2:17 pm-8:49 pm

1 stop7h 32m

$237

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 9/12

1:36 pm-10:07 pm

1 stop7h 31m

Portland

Mon 9/15

2:17 pm-8:49 pm

1 stop7h 32m

$237

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/16

2:03 pm-8:11 pm

1 stop5h 08m

Portland

Tue 9/23

6:01 am-7:57 am

Nonstop2h 56m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 9/13

7:10 pm-10:43 pm

Nonstop2h 33m

Portland

Tue 9/16

6:00 am-11:06 am

1 stop6h 06m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/18

2:41 pm-8:58 pm

1 stop5h 17m

Portland

Wed 10/22

12:11 pm-2:04 pm

Nonstop2h 53m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 9/11

1:36 pm-10:07 pm

1 stop7h 31m

Portland

Tue 9/16

7:30 am-12:10 pm

1 stop5h 40m

$243

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 10/27

10:53 am-2:12 pm

Nonstop2h 19m

Portland

Sat 11/1

4:51 pm-6:52 pm

Nonstop3h 01m

$245

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 9/12

8:30 pm-11:59 pm

Nonstop2h 29m

Portland

Tue 9/16

12:21 pm-2:14 pm

Nonstop2h 53m

$245

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 10/19

7:58 am-11:28 am

Nonstop2h 30m

Portland

Wed 10/22

6:14 am-8:08 am

Nonstop2h 54m

$245

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 9/26

8:30 pm-11:59 pm

Nonstop2h 29m

Portland

Wed 10/1

6:20 am-8:16 am

Nonstop2h 56m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 18 results
1
2

Best time to book a flight from O'Hare Intl to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Portland

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Portland. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Portland, Maine, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $296). Flying from Chicago O'Hare Intl Airport to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to PWM?

Find hourly flight availability from O'Hare Intl to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

When flying from Chicago O'Hare Intl Airport to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 19% versus a flight in the afternoon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Portland. Price data was last updated on August 17, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Tuesday evenings when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Portland, Maine

Explore weekly flight availability from O'Hare Intl to Portland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 18, 2025.

The most flights from ORD to PWM are scheduled on a Monday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated August 18, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Portland, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,925 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 6 inbound flights from Chicago O'Hare Intl per day. 3 airlines have flights to Portland from Chicago O'Hare Intl on a regular basis.

  • How long is the flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Departing from Chicago O'Hare Intl Airport to Portland, Maine will take you 5h 08m. There are 897 mi between Chicago O'Hare Intl Airport and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Portland, Maine round-trip?

    According to our current data, Delta ($163), United Airlines ($225), and American Airlines ($230) offers the cheapest pricing from Chicago O'Hare Intl Airport to Portland, Maine. You may be able to fly from Chicago O'Hare Intl Airport to Portland, Maine for 59% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Portland, Maine?

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Portland, Maine are Envoy Air (83%), Air New Zealand (65%) and American Airlines (63%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Portland, Maine?

    While on average a flight from Chicago O'Hare Intl Airport to Portland, Maine is generally $447, our data shows the cheapest flight currently is $99. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $225 for that flight.

  • Can I find deals for flights from O'Hare Intl to Portland that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Portland.

  • Can I find deals for business class flights from O'Hare Intl to Portland?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $296). Flying from Chicago O'Hare Intl Airport to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Brunswick
North Conway
Auburn
Conway
Lewiston

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Top 3 airlines flying from O'Hare Intl to Portland

Discover the top 3 airlines that operate flights from O'Hare Intl to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$225Average$391FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$230Average$344FlexibilityNo cancel feeOn-time71%

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